Triethylamine → n-Propyl (2Z)-3-amino-2-cyano-4-[(methylsulfanyl)methyl]-2-hexenoate
Reaction equation
[CH2:1]([O:4][C:5](=[O:17])[C:6]([C:15]#[N:16])=[C:7](O)[CH:8]([CH2:11][S:12][CH3:13])[CH2:9][CH3:10])[CH2:2][CH3:3].O=P(Cl)(Cl)Cl.C([N:25](CC)CC)C>C(Cl)Cl>[NH2:25]/[C:7](/[CH:8]([CH2:11][S:12][CH3:13])[CH2:9][CH3:10])=[C:6](/[C:15]#[N:16])\[C:5]([O:4][CH2:1][CH2:2][CH3:3])=[O:17]Participants
5
Conditions
- Temperature
- 25 °C
Procedure
15 g (58.3 mmol) of n-propyl-2-cyano-3-hydroxy-4-[(methyl-sulfanyl)methyl]-2-hexenoate were dissolved in CH2Cl2, and 18 g (0.12 mmol) of POCl3 were added. At 0° C., 24 g (237 mmol) of triethylamine were then added dropwise, and the mixture was stirred at 25° C. for 2 h. The reaction solution was concentrated and the residue was dissolved in acetonitrile. At 0° C., 50 ml (650 mmol) of 25% strength ammonia solution were then added dropwise to this solution, and the mixture was stirred for 1 h.
Workup
- concentrationThe reaction solution was concentrated
- dissolutionthe residue was dissolved in acetonitrile
- additionAt 0° C., 50 ml (650 mmol) of 25% strength ammonia solution were then added dropwise to this solution
- stirringthe mixture was stirred for 1 h.
Sources & evidence
- ORD record
- ord-3c75a11aa77e40e5b27fa7283f45b837
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842832B2
Reaction notes
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